CA2852607C - Utilisation d'un derive d'avermectine pour augmenter la biodisponibilite et l'efficacite des lactones macrocycliques - Google Patents

Utilisation d'un derive d'avermectine pour augmenter la biodisponibilite et l'efficacite des lactones macrocycliques Download PDF

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CA2852607C
CA2852607C CA2852607A CA2852607A CA2852607C CA 2852607 C CA2852607 C CA 2852607C CA 2852607 A CA2852607 A CA 2852607A CA 2852607 A CA2852607 A CA 2852607A CA 2852607 C CA2852607 C CA 2852607C
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compound
formula
active ingredient
medicament
group
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CA2852607A1 (fr
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Anne Lespine
Roger Prichard
Cecile Menez
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Royal Institution for the Advancement of Learning
Institut National de Recherche pour lAgriculture lAlimentation et lEnvironnement
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Royal Institution for the Advancement of Learning
Institut National de Recherche pour lAgriculture lAlimentation et lEnvironnement
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/275—Nitriles; Isonitriles
    • A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/20—Spiro-condensed systems

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Virology (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Saccharide Compounds (AREA)

Abstract

La présente invention concerne l'utilisation d'un dérivé d'avermectine en tant que médicament pour le traitement d'infections parasitaires. Le dérivé d'avermectine est représenté par la formule (I) dans laquelle : (i) R1 est sélectionné dans le groupe comprenant CH(CH3)2, CH(CH3)CH2CH3, ou cyclohexyle, (ii) X représente CH2CH2, ou CH=CH, (iii) R2 est sélectionné dans le groupe comprenant ou un groupe OH, (iv) R3 représente OH ou NOH, (v) représente une liaison simple lorsque R3 représente OH, ou une liaison double lorsque R3 représente NOH, en tant qu'inhibiteur d'une protéine membranaire qui transporte un composé exogène hors des cellules cibles.
CA2852607A 2011-10-18 2012-10-18 Utilisation d'un derive d'avermectine pour augmenter la biodisponibilite et l'efficacite des lactones macrocycliques Active CA2852607C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP11306348 2011-10-18
EP11306348.1 2011-10-18
PCT/EP2012/070704 WO2013057222A2 (fr) 2011-10-18 2012-10-18 Utilisation d'un dérivé d'avermectine pour augmenter la biodisponibilité et l'efficacité des lactones macrocycliques

Publications (2)

Publication Number Publication Date
CA2852607A1 CA2852607A1 (fr) 2013-04-25
CA2852607C true CA2852607C (fr) 2021-05-04

Family

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CA2852607A Active CA2852607C (fr) 2011-10-18 2012-10-18 Utilisation d'un derive d'avermectine pour augmenter la biodisponibilite et l'efficacite des lactones macrocycliques

Country Status (7)

Country Link
US (3) US11130776B2 (fr)
EP (2) EP2768513B8 (fr)
AU (4) AU2012324876A1 (fr)
BR (1) BR112014009406A2 (fr)
CA (1) CA2852607C (fr)
ES (1) ES2777928T3 (fr)
WO (1) WO2013057222A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103588784B (zh) * 2013-11-14 2015-12-30 大连九信生物化工科技有限公司 一种制备高纯度尼莫克汀的方法
CN108498537A (zh) * 2018-06-25 2018-09-07 塔里木大学 一种灭杀动物体外寄生虫的制剂及其制备方法

Family Cites Families (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5595756A (en) * 1993-12-22 1997-01-21 Inex Pharmaceuticals Corporation Liposomal compositions for enhanced retention of bioactive agents
US5778436A (en) 1995-03-06 1998-07-07 Duke University Predictive caching system and method based on memory access which previously followed a cache miss
WO1999063441A1 (fr) 1998-06-05 1999-12-09 Mylex Corporation Strategie de sauvegarde selective
GB9825402D0 (en) * 1998-11-19 1999-01-13 Pfizer Ltd Antiparasitic formulations
US7734591B1 (en) 1999-08-16 2010-06-08 Netapp, Inc. Coherent device to device data replication
US6434681B1 (en) 1999-12-02 2002-08-13 Emc Corporation Snapshot copy facility for a data storage system permitting continued host read/write access
AU2005202712B2 (en) 2000-03-20 2007-08-23 Elanco Us Inc. Synergistic formulations
AUPQ634300A0 (en) * 2000-03-20 2000-04-15 Eli Lilly And Company Synergistic formulations
JP3868708B2 (ja) 2000-04-19 2007-01-17 株式会社日立製作所 スナップショット管理方法及び計算機システム
AU2001278694A1 (en) * 2000-08-09 2002-02-18 The Kitasato Institute Avermectin derivatives
DK1197215T3 (da) 2000-10-10 2006-07-10 Wyeth Corp Anthelmintiske sammensætninger
US6941490B2 (en) 2000-12-21 2005-09-06 Emc Corporation Dual channel restoration of data between primary and backup servers
US6711662B2 (en) 2001-03-29 2004-03-23 Intel Corporation Multiprocessor cache coherence management
US20030064941A1 (en) * 2001-05-21 2003-04-03 Pfizer Inc. Avermectin and praziquantel combination therapy
US7296125B2 (en) 2001-11-29 2007-11-13 Emc Corporation Preserving a snapshot of selected data of a mass storage system
US7085785B2 (en) 2002-02-15 2006-08-01 International Business Machines Corporation Writable file system snapshot with ditto address feature
US7743031B1 (en) 2002-09-06 2010-06-22 3Par, Inc. Time and space efficient technique for creating virtual volume copies
US7165145B2 (en) 2003-07-02 2007-01-16 Falconstor Software, Inc. System and method to protect data stored in a storage system
US6959313B2 (en) 2003-07-08 2005-10-25 Pillar Data Systems, Inc. Snapshots of file systems in data storage systems
JP4466001B2 (ja) 2003-08-06 2010-05-26 株式会社日立製作所 スナップショット高速化方法
US7035881B2 (en) 2003-09-23 2006-04-25 Emc Corporation Organization of read-write snapshot copies in a data storage system
US7225210B2 (en) 2003-11-20 2007-05-29 Overland Storage, Inc. Block level data snapshot system and method
US7671034B2 (en) * 2003-12-19 2010-03-02 Merial Limited Stabilized formulation of ivermectin feed premix with an extended shelf life
US7440966B2 (en) 2004-02-12 2008-10-21 International Business Machines Corporation Method and apparatus for file system snapshot persistence
EP1632498A1 (fr) 2004-09-03 2006-03-08 Syngenta Participations AG Derivés d'avermectin, avermectin monosaccharide et avermectin aglycone
US7363435B1 (en) 2005-04-27 2008-04-22 Sun Microsystems, Inc. System and method for coherence prediction
US20070055710A1 (en) 2005-09-06 2007-03-08 Reldata, Inc. BLOCK SNAPSHOTS OVER iSCSI
US7426618B2 (en) 2005-09-06 2008-09-16 Dot Hill Systems Corp. Snapshot restore method and apparatus
US7751348B2 (en) 2005-11-04 2010-07-06 Cisco Technology, Inc. Method and system for providing a push-to-talk communication session
US7774316B2 (en) 2005-11-30 2010-08-10 Oracle International Corp. Filesystem snapshot enhancement to improve system performance
US8533409B2 (en) 2006-01-26 2013-09-10 Infortrend Technology, Inc. Method of managing data snapshot images in a storage system
US7676514B2 (en) 2006-05-08 2010-03-09 Emc Corporation Distributed maintenance of snapshot copies by a primary processor managing metadata and a secondary processor providing read-write access to a production dataset
US7757057B2 (en) 2006-11-27 2010-07-13 Lsi Corporation Optimized rollback of copy-on-write snapshot volumes
US7676510B1 (en) 2006-12-22 2010-03-09 Network Appliance, Inc. Space reservation monitoring in a fractionally reserved data storage system
US7870356B1 (en) 2007-02-22 2011-01-11 Emc Corporation Creation of snapshot copies using a sparse file for keeping a record of changed blocks
US7792802B1 (en) 2007-03-02 2010-09-07 3Par, Inc. Archiving logs with snapshots for data recovery
CA2684926C (fr) 2007-05-03 2014-09-30 Merial Limited Compositions comprenant des composes alcoxyether macrolides c-13 et composes de phenylpyrazole
US8583598B2 (en) 2007-05-29 2013-11-12 Brandeis University Device and method for enabling long-lived snapshots
US8364639B1 (en) 2007-10-11 2013-01-29 Parallels IP Holdings GmbH Method and system for creation, analysis and navigation of virtual snapshots
BRPI0705822A2 (pt) * 2007-10-25 2009-06-23 Schering Plough Saude Animal Ltda formulação injetável com ação prolongada e uso de um agente semi-sintético derivado do grupo das avermectinas, em combinação com um polìmero biodegradável
US20090187719A1 (en) 2008-01-17 2009-07-23 Inventec Corporation Data backup method for logical volume manager
MX2012001635A (es) 2009-08-07 2012-04-20 Gat Microencapsulation Ag Microcapsulas que contienen abamectina, milbemectinas, avermectinas, milbemicinas, emamectinas, ivermectinas y mectinas, lactonas macrolidos en general.
WO2011054103A1 (fr) 2009-11-09 2011-05-12 University Health Network Utilisation de combinaisons synergiques de composés d'avermectine et de composés antinéoplasiques en vue du traitement de cancers hématologiques
UA108641C2 (uk) 2010-04-02 2015-05-25 Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування
US8281096B1 (en) 2010-06-02 2012-10-02 Symantec Corporation Systems and methods for creating snapshots
WO2012030383A1 (fr) 2010-08-31 2012-03-08 Falconstor, Inc. Déduplication de données
US8880820B2 (en) 2010-09-08 2014-11-04 Novell, Inc. Techniques for using sparse files during snapshots
US8402008B2 (en) 2010-09-10 2013-03-19 International Business Machines Corporation Handling file operations with low persistent storage space
US8874524B1 (en) 2012-06-22 2014-10-28 Emc Corporation Handling copy on first write data for snapshot purposes
US9304901B2 (en) 2013-03-14 2016-04-05 Datadirect Networks Inc. System and method for handling I/O write requests
US9218139B2 (en) 2013-08-16 2015-12-22 International Business Machines Corporation Minimally disruptive virtual machine snapshots
US9298633B1 (en) 2013-09-18 2016-03-29 Emc Corporation Adaptive prefecth for predicted write requests
WO2016097313A1 (fr) * 2014-12-19 2016-06-23 Ablynx N.V. Dimères de nano-anticorps liés à de la cystéine
RU2571551C1 (ru) * 2015-04-16 2015-12-20 Закрытое акционерное общество "ПЕПТЕК" Специфическая сочетанная терапия злокачественных опухолей цитостатиком и его модификатором

Also Published As

Publication number Publication date
EP3701954A2 (fr) 2020-09-02
WO2013057222A3 (fr) 2013-08-22
US20210261594A1 (en) 2021-08-26
EP2768513A2 (fr) 2014-08-27
AU2020260537B9 (en) 2021-11-04
AU2017219002A1 (en) 2017-09-07
WO2013057222A2 (fr) 2013-04-25
EP3701954A3 (fr) 2021-04-21
CA2852607A1 (fr) 2013-04-25
US20180265536A1 (en) 2018-09-20
US11021508B2 (en) 2021-06-01
BR112014009406A2 (pt) 2017-04-18
AU2020260537B2 (en) 2021-10-21
AU2020260537A1 (en) 2020-11-26
EP2768513B8 (fr) 2020-05-20
EP2768513B1 (fr) 2019-12-25
AU2019204133A1 (en) 2019-07-04
US11130776B2 (en) 2021-09-28
AU2012324876A1 (en) 2014-05-01
NZ623929A (en) 2016-09-30
US20140256619A1 (en) 2014-09-11
ES2777928T3 (es) 2020-08-06

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